It is believed that he was the one who rigged the 1919 World Series and started the 'Black Sox' scandal that almost ruined baseball.
He allegedly paid the Chicago White Sox $80,000 to throw the games so he could make a fortune betting against Chicago.
He dreamed of killing his older brother Harry.
He was obsessed with gambling.
He did criminal dealings in the middle of the street with his bodyguards.
He made a fortune off of investing in horse racing tracks and rigging the races.
He had connections in all parts of the government and used them dismiss thousands of Prohibition-era court cases.
He was shot to death after he refused to pay $320,000 he lost in a poker game (1928).
His philosophy was, 'Look out for Number One. If you don't, no one else will. If a man is dumb, someone is going to get the best of him, so why not you? If you don't, you're as dumb as he is.'
He was the stereotypical penny-pinching Jew.
He is an icon of organized crime.

Why he might not be annoying

He abstained from alcohol and tobacco.
No conclusive evidence has been found to prove that he rigged the World Series.
He maintained that he never bet on the 1919 World Series after he found out it was rigged.
The 'Great Gatsby' character 'Meyer Wolfsheim' is based off of him.
The 'Guys and Dolls' character 'Nathan Detroit' is also based off of him.
He was a millionaire before the age of thirty.
His murder was never solved.

For 2019, as of last week, Out of 2 Votes: 100% Annoying
In 2018, Out of 1 Votes: 100% Annoying
In 2017, Out of 4 Votes: 100% Annoying
In 2016, Out of 5 Votes: 60.0% Annoying
In 2015, Out of 16 Votes: 56.25% Annoying
In 2014, Out of 23 Votes: 56.52% Annoying
In 2013, Out of 29 Votes: 58.62% Annoying
In 2012, Out of 23 Votes: 78.26% Annoying
In 2011, Out of 25 Votes: 84.00% Annoying
In 2010, Out of 56 Votes: 64.29% Annoying
In 2009, Out of 69 Votes: 72.46% Annoying
In 2008, Out of 30 Votes: 80.0% Annoying
In 2007, Out of 94 Votes: 73.40% Annoying
In 2006, Out of 206 Votes: 61.17% Annoying
In 2005, Out of 110 Votes: 73.64% Annoying